Global Patent Index - EP 1258476 A1

EP 1258476 A1 2002-11-20 - Alpha-amino acid derivatives, method for their preparation and their use as dipeptidyl-peptidase IV inhibitors (DPP IV)

Title (en)

Alpha-amino acid derivatives, method for their preparation and their use as dipeptidyl-peptidase IV inhibitors (DPP IV)

Title (de)

Alpha-Aminosäure-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Dipeptidylpeptidase-IV Inhibitoren (DPP IV)

Title (fr)

Dérivés d'alpha-amino-acides, leur procédé de préparation ainsi que leur utilisation en tant qu'inhibiteurs de dipeptidyl-peptidase IV (DPP IV)

Publication

EP 1258476 A1 (FR)

Application

EP 02291192 A

Priority

FR 0106375 A

Abstract (en)

Alpha amino acid derivatives (I), their optical isomers and addition salts, are new. Alpha amino acid derivatives of formula (I), their optical isomers and addition salts, are new: A = five-membered heterocycle, optionally substituted by a cyano group; Ak = 1-6C alkylene; X = single bond or phenylene; R1, R2, R4 = H or 1-6C alkyl; Y = NR4 or CH-NO2; R3 = NO2 or CN; and provided that: (i) when Y is CH-NO2, then R3 may further be 1-6C alkyl; and (ii) when A is unsubstituted, then Ak is propylene, X is a bond, Y is NH and R3 is NO2, are excluded.

Abstract (fr)

Composé de formule (I): <IMAGE> dans laquelle : <IMAGE> <IMAGE> représente un hétérocycle azoté à 5 chaînons éventuellement substitué, Ak représente une chaîne alkylène, X représente une liaison simple ou un groupement phénylène, R1 et R2, identiques ou différents, représentent chacun un atome d'hydrogène ou un groupement alkyle, R3 représente un groupement alkyle, nitro ou cyano, Y représente NR4 ou CHNO2, R4 représente un atome d'hydrogène ou un groupement alkyle, ses tautomères lorsqu'ils existent, ses isomères optiques et ses sels d'addition à un acide pharmaceutiquement acceptable, à l'exclusion des composés pour lesquels, simultanément, <IMAGE> représente un hétérocycle azoté à 5 chaînons non substitué, Ak représente le groupement -(CH2)3-, X représente une liaison simple, Y représente NH et R3 représente le groupement nitro. Médicaments.

IPC 1-7 (main, further and additional classification)

C07D 207/16; A61K 31/40; A61K 31/426; A61P 3/10; C07D 277/04; C07D 277/06; C07D 295/18

IPC 8 full level (invention and additional information)

C07D 295/10 (2006.01); A61K 31/40 (2006.01); A61K 31/426 (2006.01); A61P 3/04 (2006.01); A61P 3/08 (2006.01); A61P 3/10 (2006.01); C07D 207/16 (2006.01); C07D 277/04 (2006.01); C07D 277/06 (2006.01); C07D 295/185 (2006.01); C07K 5/02 (2006.01)

CPC (invention and additional information)

C07D 295/185 (2013.01); C07D 207/16 (2013.01); C07D 277/04 (2013.01); C07D 277/06 (2013.01); Y02P 20/55 (2015.11)

Citation (search report)

  • [Y] WO 9627593 A1 19960912 - SOD CONSEILS RECH APPLIC [FR], et al
  • [Y] WO 9515309 A1 19950608 - FERRING BV [NL], et al
  • [Y] JIANG J D ET AL: "Inhibition of uman immunodeficiency virus type 1 infection in a T-cell line (CEM) by new dipeptidyl-peptidase IV (CD26) inhibitors", RESEARCH IN VIROLOGY, ELSEVIER, PARIS, FR, vol. 4, no. 148, 1 July 1997 (1997-07-01), pages 255 - 266, XP002074032, ISSN: 0923-2516
  • [Y] YAMADA M ET AL: "A Potent Dipeptide Inhibitor of Dipeptidyl Peptidase IV", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, OXFORD, GB, vol. 8, no. 12, 16 June 1998 (1998-06-16), pages 1537 - 1540, XP004137079, ISSN: 0960-894X
  • [Y] LI J ET AL: "AMINOACYLPYRROLIDINE-2-NITRILES: POTENT AND STABLE INHIBITORS OF DEIPEPTIDYL-PEPTIDASE 4 (CD 26)", ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, NEW YORK, US, US, vol. 323, no. 1, October 1995 (1995-10-01), pages 148 - 154, XP000965067, ISSN: 0003-9861
  • [Y] AUGUSTYNS K ET AL: "THE UNIQUE PROPERTIES OF DIPEPTIDYL-PEPTIDASE IV (DPP IV/CD26) AND THE THERAPEUTIC POTENTIAL OF DPP IV INHIBITORS", CURRENT MEDICINAL CHEMISTRY, BENTHAM SCIENCE PUBLISHERS BV, BE, vol. 6, no. 4, 1999, pages 311 - 327, XP000870290, ISSN: 0929-8673
  • [Y] ASHWORTH D M ET AL: "4-Cyanothiazolidides as very potent, stable inhibitors of dipeptidyl peptidase IV", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, OXFORD, GB, vol. 6, no. 22, 19 November 1996 (1996-11-19), pages 2745 - 2748, XP004135888, ISSN: 0960-894X

Designated contracting state (EPC)

AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

EPO simple patent family

EP 1258476 A1 20021120; EP 1258476 B1 20060628; AR 033735 A1 20040107; AT 331705 T 20060715; AU 4065402 A 20021121; AU 780480 B2 20050324; BR 0201697 A 20030506; CA 2383298 A1 20021115; CA 2383298 C 20080129; CN 1164573 C 20040901; CN 1385421 A 20021218; DE 60212759 D1 20060810; DE 60212759 T2 20070802; DK 1258476 T3 20061030; EA 004865 B1 20040826; EA 200200446 A1 20021226; ES 2266422 T3 20070301; FR 2824825 A1 20021122; FR 2824825 B1 20050506; HK 1050526 A1 20050506; HU 0201646 A2 20030228; HU 0201646 A3 20040301; HU 0201646 D0 20020729; JP 2002363157 A 20021218; JP 3798337 B2 20060719; KR 100460782 B1 20041209; KR 20020087379 A 20021122; MX PA02004642 A 20040716; NO 20022285 A 20021118; NO 20022285 D0 20020514; NO 322569 B1 20061030; NZ 518948 A 20031031; PL 353910 A1 20021118; PT 1258476 E 20061031; US 2003078247 A1 20030424; US 6706742 B2 20040316; ZA 200203867 B 20030102

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